Cheap Flights from Milan to Chicago, IL from $418

Return flight: Chicago – Milan

On Cheapflightsplus.com you will find 1 direct and 999 connecting flights from Milan to Chicago. You can compare airfare deals from 39 airlines and multiple travel sites from $418, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $418 (one-way), $717 (round-trip).
Direct flights
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Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
15:05 — 18:10
15:05 — 18:10 UA415 United Airlines
Milan — Chicago
10h 5m
Find flight
from$904
11:55 — 22:55
11:55 — 14:50 NO787 Neos
Milan — New York
6h 25m stop
21:15 — 22:55 NK225 Spirit Airlines
New York — Chicago
18h
including layover
Find flight
from$583
17:45 — 15:30
+1 day
17:45 — 19:40 TP827 TAP Portugal
Milan — Lisbon
16h 15m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
28h 45m
including layover
Find flight
from$578
06:40 — 08:51
+1 day
06:40 — 07:50 W46301 Aero Services Executive
Milan — London
6h 10m stop
14:00 — 18:45 Z0723 Z0
London — Miami
11h 45m stop
06:30 — 08:51 NK1838 Spirit Airlines
Miami — Chicago
33h 11m
including layover
Find flight
from$480
06:40 — 10:02
+1 day
06:25 — 07:35 W46301 Aero Services Executive
Milan — London
6h 10m stop
14:00 — 18:30 Z0783 Z0
London — Orlando
13h 30m stop
11:56 — 13:54 F91457 Frontier Airlines
Orlando — Chicago
34h 22m
including layover
Find flight
from$485
07:15 — 20:08
07:00 — 10:35 U23969 EasyJet
Milan — Reykjavik
4h 30m stop
15:20 — 17:00 OG101 Air Onix
Reykjavik — Baltimore
2h 9m stop
16:20 — 17:27 F93087 Frontier Airlines
Baltimore — Chicago
19h 53m
including layover
Find flight
from$423
08:55 — 10:05
+1 day
08:55 — 10:25 VY8433 Vueling
Milan — Paris
8h 15m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — New York
11h 35m stop
08:35 — 10:05 NK779 Spirit Airlines
New York — Chicago
32h 10m
including layover
Find flight
from$509
08:55 — 13:44
+1 day
08:55 — 10:25 VY8433 Vueling
Milan — Paris
8h 15m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — Newark
15h 8m stop
12:08 — 13:44 NK329 Spirit Airlines
Newark — Chicago
35h 49m
including layover
Find flight
from$545
09:40 — 22:55
09:40 — 10:50 W96305 Wizz Air UK
Milan — London
2h 10m stop
13:00 — 15:50 Z0701 Z0
London — New York
5h 25m stop
21:15 — 22:55 NK225 Spirit Airlines
New York — Chicago
20h 15m
including layover
Find flight
from$444
09:40 — 11:02
+1 day
09:40 — 10:50 W96305 Wizz Air UK
Milan — London
2h 10m stop
13:00 — 15:50 Z0701 Z0
London — Newark
17h 36m stop
09:26 — 11:02 NK209 Spirit Airlines
Newark — Chicago
32h 22m
including layover
Find flight
from$484
10:30 — 08:51
+1 day
10:30 — 12:15 U25064 EasyJet
Milan — Berlin
3h 15m stop
15:30 — 20:10 N0623 N0
Berlin — Miami
10h 20m stop
06:30 — 08:51 NK1838 Spirit Airlines
Miami — Chicago
29h 21m
including layover
Find flight
from$460
10:55 — 10:17
+1 day
10:55 — 12:35 W46339 Aero Services Executive
Milan — Paris
6h 5m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — New York
11h 36m stop
08:36 — 10:17 NK779 Spirit Airlines
New York — Chicago
30h 22m
including layover
Find flight
from$478
11:45 — 22:52
+1 day
11:45 — 13:15 U23807 EasyJet
Milan — Paris
5h 25m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — Newark
24h 15m stop
21:15 — 22:52 NK329 Spirit Airlines
Newark — Chicago
42h 7m
including layover
Find flight
from$533
13:15 — 00:34
+2 days
13:15 — 14:45 U24544 EasyJet
Milan — Paris
5h 15m stop
20:00 — 22:05 N0301 N0
Paris — Newark
24h 50m stop
22:55 — 00:34 NK329 Spirit Airlines
Newark — Chicago
42h 19m
including layover
Find flight
from$418
13:30 — 17:09
+2 days
13:30 — 17:15 W46453 Aero Services Executive
Milan — Reykjavik
22h 5m stop
15:20 — 17:00 OG101 Air Onix
Reykjavik — Baltimore
23h 8m stop
16:08 — 17:09 F93087 Frontier Airlines
Baltimore — Chicago
58h 39m
including layover
Find flight
from$450
15:00 — 00:34
+2 days
15:00 — 16:10 AZ2071 Alitalia
Milan — Rome
3h stop
19:10 — 22:30 N0401 N0
Rome — Newark
24h 25m stop
22:55 — 00:34 NK329 Spirit Airlines
Newark — Chicago
40h 34m
including layover
Find flight
from$439
15:00 — 10:17
+1 day
15:00 — 16:10 AZ2071 Alitalia
Milan — Rome
3h stop
19:10 — 22:30 N0401 N0
Rome — New York
10h 6m stop
08:36 — 10:17 NK779 Spirit Airlines
New York — Chicago
26h 17m
including layover
Find flight
from$486
16:00 — 10:07
+1 day
16:00 — 17:10 AZ2059 Alitalia
Milan — Rome
2h stop
19:10 — 22:30 N0401 N0
Rome — New York
10h 5m stop
08:36 — 10:17 NK779 Spirit Airlines
New York — Chicago
25h 7m
including layover
Find flight
from$512
16:55 — 15:30
+1 day
16:55 — 18:30 VY6333 Vueling
Milan — Barcelona
2h 40m stop
21:10 — 22:10 TP1039 TAP Portugal
Barcelona — Lisbon
13h 45m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
29h 35m
including layover
Find flight
from$547
18:35 — 14:33
+2 days
18:35 — 19:45 W46303 Aero Services Executive
Milan — London
16h 15m stop
12:00 — 16:45 Z0723 Z0
London — Miami
19h 15m stop
12:00 — 14:33 NK396 Spirit Airlines
Miami — Chicago
50h 58m
including layover
Find flight
from$458
18:35 — 11:02
+2 days
18:35 — 19:45 W46303 Aero Services Executive
Milan — London
17h 15m stop
13:00 — 15:50 Z0701 Z0
London — Newark
17h 36m stop
09:26 — 11:02 NK209 Spirit Airlines
Newark — Chicago
47h 27m
including layover
Find flight
from$475
19:10 — 11:02
+2 days
19:10 — 20:20 BA585 British Airways
Milan — London
16h 40m stop
13:00 — 15:50 Z0701 Z0
London — Newark
17h 36m stop
09:26 — 11:02 NK209 Spirit Airlines
Newark — Chicago
46h 52m
including layover
Find flight
from$542
20:15 — 10:05
+2 days
20:15 — 21:45 VY8431 Vueling
Milan — Paris
22h 15m stop
20:00 — 22:05 N0301 N0
Paris — New York
10h 30m stop
08:35 — 10:05 NK779 Spirit Airlines
New York — Chicago
44h 50m
including layover
Find flight
from$438
20:45 — 12:39
+2 days
20:45 — 22:15 VY8431 Vueling
Milan — Paris
20h 25m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — New York
13h 59m stop
10:59 — 12:39 NK1681 Spirit Airlines
New York — Chicago
46h 54m
including layover
Find flight
from$497
21:05 — 10:05
+2 days
21:05 — 22:40 TO3949 Transavia France
Milan — Paris
21h 20m stop
20:00 — 22:05 N0301 N0
Paris — New York
10h 30m stop
08:35 — 10:05 NK779 Spirit Airlines
New York — Chicago
44h
including layover
Find flight
from$438
21:55 — 12:39
+2 days
21:55 — 23:30 U24546 EasyJet
Milan — Paris
19h 10m stop
18:40 — 21:00 BF720 Bluebird Cargo
Paris — New York
13h 59m stop
10:59 — 12:39 NK1681 Spirit Airlines
New York — Chicago
45h 44m
including layover
Find flight
from$475
22:05 — 14:33
+2 days
22:05 — 23:05 U22486 EasyJet
Milan — London
12h 55m stop
12:00 — 16:45 Z0723 Z0
London — Miami
19h 15m stop
12:00 — 14:33 NK396 Spirit Airlines
Miami — Chicago
47h 28m
including layover
Find flight
from$469
22:15 — 10:17
+2 days
22:15 — 01:30 W43064 Aero Services Executive
Milan — Bucharest
8h 5m stop
09:35 — 12:25 H4101 Heli Securite
Bucharest — New York
20h 11m stop
08:36 — 10:17 NK779 Spirit Airlines
New York — Chicago
43h 2m
including layover
Find flight
from$470
*Departure and arrival times - local. Updated on May 9, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 03:15 to 23:40 from 4 Milan airports and arrive 03:15 to 23:40 to 7 Chicago airports. Average flight time is 10h 5m.

  • The fastest flight 10h 5m
  • Average flight time 10h 5m
  • The earliest flight 03:15
  • The latest flight 23:40
  • Distance 4530 ml

The cheapest months to travel to Chicago are december (from 418 $), february (from 423 $), november (from 438 $).

The most expensive months are january (from 444 $), november (from 438 $), february (from 423 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $418. This airfare is for economy class on one-way U24544 flight by EasyJet for December 12, 2024 which leaves Malpensa in Milan at 13:15 am and arrives at Chicago O'Hare International at 00:34.

Economy class
$418
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Business class
?
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First class
?
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Popular Airlines on the Route

The flight Milan — Chicago is served by 39 regular airlines and 8 low-cost airlines. Most of the flights on this route are operated by Neos - 11 departures per week at the price of from $ 583 . And the most expensive tickets are offered by United Airlines airline - from $ 1833.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA415 by United Airlines takes 10h 5m and the cheapest is U24544 by EasyJet for $904.

  • UA - United Airlines
    from $904
    Find
See more direct flights

Connecting Flights

There are 999 flights with layovers on the route. The fastest connecting flight is UA9305 by United Airlines takes 11h 45m and the cheapest is U24544 by EasyJet for $418.

  • NO - Neos
    from $583
    Find
  • S4 - SATA International
    from $660
    Find
  • W9 - Wizz Air UK
    from $444
    Find
  • XZ - Ivoire Aero-Services
    from $801
    Find
  • VY - Vueling
    from $438
    Find
  • FI - Icelandair
    from $899
    Find
  • LO - LOT
    from $1022
    Find
  • BJ - Nouvelair Tunisie
    from $760
    Find
  • JU - Air Serbia
    from $615
    Find
  • LX - SWISS International Air Lines
    from $672
    Find
  • UA - United Airlines
    from $677
    Find
  • DY - Norwegian
    from $602
    Find
See more connecting flights

Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

  • Linate-LIN
    from $439
    Find
  • Malpensa-MXP
    from $418
    Find
  • Milan Bergamo (Orio al Serio)-BGY
    from $541
    Find
  • Segrate-SWK
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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